US2960509A - Trimellitic imide-amide - Google Patents

Trimellitic imide-amide Download PDF

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Publication number
US2960509A
US2960509A US800641A US80064159A US2960509A US 2960509 A US2960509 A US 2960509A US 800641 A US800641 A US 800641A US 80064159 A US80064159 A US 80064159A US 2960509 A US2960509 A US 2960509A
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trimellitic
amide
triamide
amide imide
solution
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US800641A
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James R Stephens
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Standard Oil Co
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Standard Oil Co
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Priority to US800641A priority Critical patent/US2960509A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide

Definitions

  • This invention relates to the novel compound trimellitic amide imide and to a method of preparation thereof.
  • Trimellitic amide imide may also be called 4-carbamylphthalimide.
  • a simple structural configuration of this compound is set out below:
  • Trimellitic amide imide is readily prepared from tri mellitic triamide by heating said triamide to its decomposition temperature wherein upon the trimellitic amide imide is formed, however, it is preferred to prepare the trimellitic amide imide by contacting trimellitic triamide with liquid water at a temperature from about 80 C. to about 120 C. The contacting between the triamide and the liquid water is continued until the triamide has passed into solution in said water. The triamide decomposes and the material which goes into solution is the trimellitic amide imide; ammonia is evolved from the reaction zone showing that conversion of the trimellitic triamide is taking place.
  • the trimellitic amide imide may be recovered HzN O C- 2,960,509 Patented Nov. 15, 1960 "ice by distilling ofi the water or by cooling the water solution until the solute precipitates out of solution.
  • the solid prepared by this method melted at 312 C. on the FischerJohns stage. Infrared inspection of the solid concurs with the amide imide configuration.
  • Trimellitic amide imide reacts with formaldehyde to form N-methylolated derivatives, which can be used as such, or preferably, with the addition of inert fillers, in the preparation of thermoset resin articles.
  • a method for preparing trimellitic amide imide which method comprises intermingling liquid water and trimellitic triamide at a temperature from about 80 C. to about C. until ammonia ceases to be evolved indicating essentially complete decomposition of said triamide to trimellitic amide imide, suflicient liquid water being present to dissolve all of said amide imide product and removing water to obtain a solid trimellitic amide imide product.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Description

United States Patent TRIMELLITIC HVIIDE-AMIDE James R. Stephens, Gary, Ind., assignor to Standard Oil Company, Chicago, 111., a corporation of Indiana No Drawing. Filed Mar. 20, 1959, Ser. No. 800,641
2 Claims. (Cl. 260-326) This invention relates to the novel compound trimellitic amide imide and to a method of preparation thereof.
Trimellitic amide imide may also be called 4-carbamylphthalimide. A simple structural configuration of this compound is set out below:
Trimellitic amide imide is readily prepared from tri mellitic triamide by heating said triamide to its decomposition temperature wherein upon the trimellitic amide imide is formed, however, it is preferred to prepare the trimellitic amide imide by contacting trimellitic triamide with liquid water at a temperature from about 80 C. to about 120 C. The contacting between the triamide and the liquid water is continued until the triamide has passed into solution in said water. The triamide decomposes and the material which goes into solution is the trimellitic amide imide; ammonia is evolved from the reaction zone showing that conversion of the trimellitic triamide is taking place. The trimellitic amide imide may be recovered HzN O C- 2,960,509 Patented Nov. 15, 1960 "ice by distilling ofi the water or by cooling the water solution until the solute precipitates out of solution.
Example Trimellitic triamide, 3.7 grams, and ml. of water were boiled until all of the trimellitic triamide had passed into solution and evolution of ammonia had ceased. The solution was concentrated by boiling until solid material could be precipitated from solution when the solution was cooled to room temperature, about 25 C. The solid precipitate was recovered by filtration and dried.
The solid prepared by this method melted at 312 C. on the FischerJohns stage. Infrared inspection of the solid concurs with the amide imide configuration.
Trimellitic amide imide reacts with formaldehyde to form N-methylolated derivatives, which can be used as such, or preferably, with the addition of inert fillers, in the preparation of thermoset resin articles.
This is a continuation-in-part of my co-pending application Serial No. 799,839, filed March 17, 1959.
Thus having described the invention, what is claimed is:
1. Trimellitic amide imide.
2. A method for preparing trimellitic amide imide which method comprises intermingling liquid water and trimellitic triamide at a temperature from about 80 C. to about C. until ammonia ceases to be evolved indicating essentially complete decomposition of said triamide to trimellitic amide imide, suflicient liquid water being present to dissolve all of said amide imide product and removing water to obtain a solid trimellitic amide imide product.
References Cited in the file of this patent Perkin et al., J. Chem. Soc. (London), vol. 127 (1925) pp. 2294-2295.

Claims (1)

1. TRIMELLITIC AMIDE IMIDE.
US800641A 1959-03-20 1959-03-20 Trimellitic imide-amide Expired - Lifetime US2960509A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3246009A (en) * 1963-08-27 1966-04-12 Smith Kline French Lab Trifluoromethylphthalimides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3246009A (en) * 1963-08-27 1966-04-12 Smith Kline French Lab Trifluoromethylphthalimides

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